ES2661262T3 - Nuevo procedimiento de síntesis de agomelatina - Google Patents

Nuevo procedimiento de síntesis de agomelatina Download PDF

Info

Publication number
ES2661262T3
ES2661262T3 ES14821794.6T ES14821794T ES2661262T3 ES 2661262 T3 ES2661262 T3 ES 2661262T3 ES 14821794 T ES14821794 T ES 14821794T ES 2661262 T3 ES2661262 T3 ES 2661262T3
Authority
ES
Spain
Prior art keywords
formula
compound
methoxynaphthalen
iii
synthesis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
ES14821794.6T
Other languages
English (en)
Spanish (es)
Inventor
Jean-François Briere
Raphaël LEBEUF
Vincent Levacher
Christophe Hardouin
Jean-Pierre Lecouve
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Les Laboratoires Servier SAS
Original Assignee
Les Laboratoires Servier SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Les Laboratoires Servier SAS filed Critical Les Laboratoires Servier SAS
Application granted granted Critical
Publication of ES2661262T3 publication Critical patent/ES2661262T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B43/00—Formation or introduction of functional groups containing nitrogen
    • C07B43/06—Formation or introduction of functional groups containing nitrogen of amide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C07C231/065—By hydration using metals or metallic ions as catalyst
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/32—Preparation of ethers by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/92—Naphthofurans; Hydrogenated naphthofurans

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Inorganic Compounds Of Heavy Metals (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
ES14821794.6T 2013-12-05 2014-12-04 Nuevo procedimiento de síntesis de agomelatina Active ES2661262T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1362198A FR3014437B1 (fr) 2013-12-05 2013-12-05 Nouveau procede de synthese de l'agomelatine
FR1362198 2013-12-05
PCT/FR2014/053157 WO2015082847A1 (fr) 2013-12-05 2014-12-04 Nouveau procede de synthese de l'agomelatine

Publications (1)

Publication Number Publication Date
ES2661262T3 true ES2661262T3 (es) 2018-03-28

Family

ID=50482958

Family Applications (1)

Application Number Title Priority Date Filing Date
ES14821794.6T Active ES2661262T3 (es) 2013-12-05 2014-12-04 Nuevo procedimiento de síntesis de agomelatina

Country Status (27)

Country Link
US (1) US9604911B2 (fr)
EP (1) EP3077354B1 (fr)
JP (1) JP2017504580A (fr)
KR (1) KR20160093698A (fr)
CN (1) CN105793224B (fr)
AU (1) AU2014358965B2 (fr)
CA (1) CA2932193C (fr)
CY (1) CY1121116T1 (fr)
DK (1) DK3077354T3 (fr)
EA (1) EA030800B1 (fr)
ES (1) ES2661262T3 (fr)
FR (1) FR3014437B1 (fr)
HR (1) HRP20180251T1 (fr)
HU (1) HUE036562T2 (fr)
LT (1) LT3077354T (fr)
MA (1) MA39063B1 (fr)
MD (1) MD20160071A2 (fr)
ME (1) ME02968B (fr)
MX (1) MX2016007186A (fr)
NO (1) NO3077354T3 (fr)
PL (1) PL3077354T3 (fr)
PT (1) PT3077354T (fr)
RS (1) RS56768B1 (fr)
RU (1) RU2683279C1 (fr)
SI (1) SI3077354T1 (fr)
WO (1) WO2015082847A1 (fr)
ZA (1) ZA201603457B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106831467B (zh) * 2016-12-08 2019-03-01 江苏豪森药业集团有限公司 阿戈美拉汀的制备方法
CN107033011B (zh) * 2017-05-18 2018-07-17 郑州职业技术学院 2-(7-甲氧基-1-萘基)乙胺的制备方法
CN107353229B (zh) * 2017-08-08 2019-04-30 许昌恒生制药有限公司 一种阿戈美拉汀中间体的制备方法
CN114560785B (zh) * 2022-03-04 2023-06-13 郑州大学 一种伯酰胺类化合物的合成方法
AU2024392892A1 (en) * 2023-12-06 2026-07-02 Psylo Pty Ltd Compounds active at the serotonergic 5-ht 2a receptor

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2658818B1 (fr) * 1990-02-27 1993-12-31 Adir Cie Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
FR2713636B1 (fr) * 1993-12-07 1996-01-05 Adir Nouveaux dérivés naphtaléniques, leur procédé de préparation, et les compositions pharmaceutiques qui les contiennent.
FR2771739B1 (fr) * 1997-11-28 2001-04-20 Adir Nouveaux composes naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JP4798924B2 (ja) * 1999-12-13 2011-10-19 中外製薬株式会社 ヒドロキシカルボニル−ハロゲノアルキル側鎖を有する化合物
EA012262B1 (ru) * 2004-01-22 2009-08-28 Эли Лилли Энд Компани Селективные модуляторы рецепторов эстрогена для лечения вазомоторных симптомов
FR2866335B1 (fr) * 2004-02-13 2006-05-26 Servier Lab Nouveau procede de synthese de l'agomelatine
CN101638376B (zh) * 2008-07-29 2011-04-27 江苏恩华药业股份有限公司 阿戈美拉汀的制备方法及其中间体
FR2934855B1 (fr) * 2008-08-05 2010-08-13 Servier Lab Nouveau procede de synthese de l'agomelatine
FR2934857B1 (fr) 2008-08-05 2010-08-27 Servier Lab Nouveau procede de synthese de l'agomelatine
FR2934859B1 (fr) * 2008-08-05 2010-08-13 Servier Lab Nouveau procede de synthese de l'agomelatine

Also Published As

Publication number Publication date
CN105793224B (zh) 2018-07-06
PL3077354T3 (pl) 2018-04-30
AU2014358965B2 (en) 2018-08-16
NO3077354T3 (fr) 2018-04-28
US20160368859A1 (en) 2016-12-22
MA39063A1 (fr) 2018-08-31
EA201600440A1 (ru) 2016-11-30
EP3077354A1 (fr) 2016-10-12
AU2014358965A1 (en) 2016-06-09
DK3077354T3 (en) 2018-02-26
JP2017504580A (ja) 2017-02-09
US9604911B2 (en) 2017-03-28
WO2015082847A1 (fr) 2015-06-11
MX2016007186A (es) 2016-07-21
MA39063B1 (fr) 2020-03-31
FR3014437A1 (fr) 2015-06-12
CA2932193C (fr) 2018-07-17
SI3077354T1 (en) 2018-03-30
EP3077354B1 (fr) 2017-11-29
ME02968B (fr) 2018-07-20
ZA201603457B (en) 2019-11-27
KR20160093698A (ko) 2016-08-08
PT3077354T (pt) 2017-12-26
EA030800B1 (ru) 2018-09-28
HRP20180251T1 (hr) 2018-03-09
HUE036562T2 (hu) 2018-07-30
CN105793224A (zh) 2016-07-20
FR3014437B1 (fr) 2016-12-23
MD20160071A2 (ro) 2016-11-30
RS56768B1 (sr) 2018-04-30
CA2932193A1 (fr) 2015-06-11
RU2683279C1 (ru) 2019-03-27
CY1121116T1 (el) 2019-12-11
LT3077354T (lt) 2018-02-12

Similar Documents

Publication Publication Date Title
RU2683279C1 (ru) Новый способ синтеза агомелатина
CN103435575A (zh) 1-（ 3-（ 3-（ 4-氯苯基）丙氧基）丙基）哌啶盐酸盐的制备方法
CN110668951A (zh) 一种盐酸司来吉兰的合成工艺
EP3081554B1 (fr) Procédé pour la préparation de silodosine et intermédiaire correspondant
CN104387282B (zh) 一种氘代莱克多巴胺的制备方法
JP2022055368A (ja) ベンゾアゼピン誘導体の製造方法及びその中間体
CN109942442A (zh) 一种盐酸达泊西汀有关物质i的制备方法
ES2668527T3 (es) Nuevo procedimiento de síntesis de 7-metoxinaftalen-1-carbaldehído y utilización en la síntesis de agomelatina
HK1229786A1 (en) Novel method for the synthesis of agomelatine
CN103553940A (zh) 一种新晶型盐酸他喷他多的制备方法
ES2564959T3 (es) Nuevo procedimiento de síntesis de 3-(2-bromo-4,5-dimetoxifenil)propanonitrilo y su aplicación a la síntesis de ivabradina y de sus sales de adición de un ácido farmacéuticamente aceptable
CN105111086A (zh) 一种1-苯基-2-硝基乙醇及其衍生物的制备方法
HK1229786B (en) Novel method for the synthesis of agomelatine
ITMI980284A1 (it) Processo per la preparazione dell'acido 3-[4-(1-h-imidazol-1-il- metil]-2 propenoico ed i suoi sali
HK1226387A1 (en) Novel method for the synthesis of agomelatine
JP4330270B2 (ja) 新規製造法
Zheng et al. A Now Asymmetric Synthesis of (R)-3-Methylpyrrolidine Alkaloids Starting from (S)-Malic Acid
JP4995172B2 (ja) 糖脂質誘導体、その製造方法並びにそれを有効成分とする医薬
JPS62145037A (ja) 光学活性α，β−二基置換カルボニル化合物の立体選択性製造方法
HK1229785B (en) Novel method for the synthesis of 7-methoxy-naphthalene-1-carbaldehyde and use thereof in the synthesis of agomelatine
WO2002088072A1 (fr) Procede de preparation de composes d'alkylene
HK1229785A1 (en) Novel method for the synthesis of 7-methoxy-naphthalene-1-carbaldehyde and use thereof in the synthesis of agomelatine
JPS61221184A (ja) ２−（２−チエニル）−エチルアミンの製造方法
JP2010001291A (ja) 糖脂質誘導体の製造方法
CN103553962A (zh) 合成n-（1-取代苯基）烷基羟胺衍生物的盐的制备方法